Triethylamine → N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

HRID 413977노트

반응식

HRID 413977 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH2:17])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:28])=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20].C(N(CC)CC)C>C(Cl)Cl>[ClH:28].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:18])[CH2:14][CH2:15][CH2:16][NH:17][C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 104449491,3-Propanediamine, N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-

생성물 1

HCID 70011353N-[3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]propyl]4-nitrobenzamide hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

800 mg (3.17 mmol) N-[2-(3,4-Dimethoxyphenyl)ethyl]-N-methyl-1,3-propanediamine (D2), 630 mg (3.33 mmol) 4-nitro benzoyl chloride and 0.35 g (3.49 mmol) triethylamine in 30 ml methylene chloride were stirred for 2 hours at room temperature. The mixture was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified twice by chromatography on silicagel using methylene chloride/methanol: 97/3 then 94/6 yielding 700 mg (55%) of the desired compound as a base. The compound was salified in methylene chloride by adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid: mp =80-90° C.

후처리

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified twice by chromatography on silicagel
  5. additionby adding a solution of hydrochoric acid in diethyl ether yielding 594 mg (43%) of the desired compound as a yellow solid
  6. custommp =80-90° C.

출처 및 근거

ORD 기록
ord-d6eae474955f41c498ddd5ef34d0c9de
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06570037B2

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